129-64-6Relevant articles and documents
Synthesis, structures, molecular docking, cytotoxicity and bioimaging studies of two novel Zn(II) complexes
Gao, Enjun,Sun, Na,Zhang, Shaozhong,Ding, Yuqing,Qiu, Xue,Zhan, Yang,Zhu, Mingchang
, p. 1 - 11 (2016)
Two novel compounds [Zn2(Endc)2(bipy)2(H2O)3]·4(H2O)·2(O)(1), [Zn2(Endc)2(phen)2(H2O)]·(O)(2) (bipy Combining double low line 2,2-bipyridine, phen Combining double low line 1,10-phenanthroline, and Endc Combining double low line endo-norbornene-cis-5,6-dicarboxylicacid) have been synthesized and characterized. In this paper abbreviations are FS-DNA (fish sperm DNA), HeLa (human cervix epithelia carcinoma cells), KB (human oral epithelial carcinoma cells), LO2 (human liver cell L-O2), EtBr (ethidium bromide), DMF (Dimethyl Formamide), MTT ([3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium]). The binding of complexes with Fish Sperm DNA were measured by electronic absorption spectra and fluorescence spectroscopy. The ability of these complexes to cleave the pBR322 plasmid DNA or the KB and HeLa DNA extracted in our laboratory was demonstrated by gel electrophoresis assay. The cytotoxic effects of these complexes were examined on two tumor cell lines, HeLa, KBr and one normal cell line LO-2. UV absorption and fluorescence spectra indicate the ability of the complexes bond to DNA with different binding affinity. Gel electrophoresis assay demonstrates which one complex more effective DNA-cleavage activity. The cytotoxic activity of the complexes was tested against two different cancer and one normal cell lines. The two complexes exhibited cytotoxic specificity and significant cancer cell inhibitory rate and lower cytotoxicity toward the normal cell lines. The unique interaction mode with DNA and cancer cells inhibition effect clearly revealed the relationship between the structure and the activity of the novel antitumor agent Zn(II) complexes.
Synthesis of new polyhedral oligomeric silsesquioxane derivatives as some possible antimicrobial agents
Ersoy, Elif Basak,Gunkara, Omer Tahir,Ocal, Nuket
, p. 257 - 268 (2019)
1,3-Dipolar cycloaddition reactions were studied to synthesize Polyhedral oligomeric silsesquioxane (POSS)-based norbornyl imide derivatives containing izoxazoline groups in good yields. And also 1,3-dipolar cycloaddition reactions of azomethine ylides with POSS-based norbornene dipolarophiles for a synthesis of the novel POSS-based norbornane-fused spiro-1,3-indandionolylpyrrolidines are reported. All newly synthesized POSS compounds were structurally characterized by FTIR, 1H, 13C NMR, HRMS and GC/MS analyses.
An analysis of the structural, thermal and optical characteristics as well as the electrical resistivity of tert-butyldiphenylsilyl substituted poly(norbornene-dicarboximide)s
Spring, Andrew M.,Maeda, Daisuke,Ozawa, Masaaki,Odoi, Keisuke,Qiu, Feng,Yamamoto, Kazuhiro,Yokoyama, Shiyoshi
, p. 189 - 198 (2015)
A sequence of well controlled tert -butyldiphenylsilyl substituted poly(norbornene-dicarboximide)s with ascending molecular weights have been prepared using the Grubbs 1st generation catalyst in anhydrous chloroform. The kinetics of the polymerization was examined using nuclear magnetic resonance spectroscopy and gel permeation chromatography. By decreasing the Grubbs catalyst concentration, the polymer molecular weights increased linearly. The glass transition temperatures and thermal decomposition temperatures initially increased with polymer molecular weight, then reached a plateau. Regardless of molecular weight the polydispersities remained narrow. The polymers exhibited a predominantly trans microstructure and matrix-assisted laser desorption/ionization mass spectrometry was utilized to determine polymer end groups and to calculate the absolute molecular weights. The residual ruthenium content of the polymers was quantified using inductively coupled plasma mass spectrometry and the influence on the resistivity, refractive indices and thin film optical transmittance was evaluated.
ROMP polymer-based antimicrobial films repeatedly chargeable with silver ions
Takano, Shigenaga,Tamegai, Hideyuki,Itoh, Toshihiro,Ogata, Seitaro,Fujimori, Hiroki,Ogawa, Shoujiro,Iida, Takashi,Wakatsuki, Yasuo
, p. 195 - 203 (2011)
Two norbornene derivatives bearing a pendant pyridyl group were prepared: the 3-(pyridin-2-yl)propyl ester of 5-norbornene-endo-2-carboxylic acid (1) and N-(pyridin-2-ylmethyl)-5-norbornene-endo-2,3-dicarboxyimide (2). Both of these compounds produced high yields of ROMP polymers, poly(1) and poly(2), with the 2nd generation Grubbs catalyst. When Ag+ ions were added to these polymer solutions, the polymer-Ag+ composites, poly(1-Ag) and poly(2-Ag), were formed quantitatively. Poly(2) and poly(2-Ag) produced films from their DMF solutions, and the latter film showed strong antimicrobial properties against Gram-positive Bacillus subtilis and Gram-negative Escherichia coli. Alternatively, when the film of poly(2) was immersed in a solution of Ag+, it was able to trap the ion to give a surface-modified film [Ag/poly(2)]. The antimicrobial efficacy of [Ag/poly(2)] was the same as that of films made of poly(2-Ag), which indicated that the solid-state reaction of the film surfaces toward Ag+ ions in solution was quantitative. When the [Ag/poly(2)] film lost its biocidal effect after repeated use, the Ag + ions could be reloaded by immersing the film in a silver ion solution, which fully restored original activity.
Gas sorption in new fluorine containing polynorbornenes with imide side chain groups
Tlenkopatchev, Mikhail,Vargas, Joel,Almaraz-Giron, Marco A.,Lopez-Gonzalez, Mar,Riande, Evaristo
, p. 2696 - 2703 (2005)
The synthesis of (N-3,5-bis(trifluoromethyl)phenyl-exo-endo-norbornene-5,6-dicarboximide) as well as the ring opening methatesis polymerization (ROMP) of this monomer to yield poly(N-3,5-bis-(trifluoromethyl)phenyl-exo-encdo-norbornene-5,6-dicarboximide) are reported. The glass transition of the polymer is 162°C. Solubility coefficients of different gases (nitrogen, oxygen, carbon monoxide, carbon dioxide, methane, ethane, ethylene, propane, and propylene) in membranes prepared by casting from poly(N-3,5-bis(trifluoromethyl)phenyl-exo-endo-norbornene-5,6-dicarboximide) solutions were measured at several temperatures and pressures. The interpretation of the sorption results by the dual-mode model gives the Henry and Langmuir contributions to the solubility. As usual in glassy membranes, sorption processes are exothermic and the activation energies associated with the Henry and Langmuir parameters are also negative. Gas sorption in the continuous amorphous phase was interpreted in terms of the Flory-Huggins theory obtaining reasonable values for the enthalpic parameter x that accounts for the gas (in liquid form)-polymer interactions. The use of this approach to simulate gas sorption in polymers is discussed.
Synthesis, characterization, DNA interaction, apoptosis and molecular docking of Cu(II) and Mn(II) complexes with endo-norbornene-cis-5,6-dicarboxylic acid
Gao, Enjun,Ding, Yuqing,Sun, Na,Zhang, Shaozhong,Qiu, Xue,Zhan, Yang,Zhu, Mingchang
, (2017)
Two new novel complexes, [Cu4(Endc)4(phen)4]?7(H2O)?2(O) and [Mn2(Endc)2(phen)2(H2O)2]?(H2O) (phen =1,10-phenanthroline, H2Endc?=?endo-norbornene-cis-5,6-dicarboxylic acid), were synthesized and structurally characterized using IR and 1H NMR spectroscopies, elemental analysis and single-crystal X-ray diffractometry. Their reactivity with calf thymus DNA and HeLa cell DNA was measured using UV absorption and fluorescence spectroscopies. The results indicated that these complexes can bind to DNA with different binding affinity. Gel electrophoresis assay demonstrated the ability of the complexes to cleave pBR322 plasmid DNA. Apoptotic study showed that the complexes exhibit significant cancer cell inhibitory rates. Eventually, the complexes can suitably dock with a special DNA (PDB ID: 1AIO).
Stereoselective synthesis of polycyclic thiopyrans
Meier, Herbert,Schmidt, Michael,Mayer, Axel,Schollmeyer, Dieter,Beile, Bernhard
, p. 516 - 520 (2012)
The reaction of benzothiete (1) and the bicyclic alkenes 5, 7, 9, or 12 shows a very high π side selectivity (de > 95%) in the formation of the polycyclic thiopyrans 6, 8, 10, 11, 13, and 14.
Protein phosphatase 2A inhibition and circumvention of cisplatin cross-resistance by novel TCM-platinum anticancer agents containing demethylcantharidin
To, Kenneth K.W.,Wang, Xinning,Yu, Chun Wing,Ho, Yee-Ping,Au-Yeung, Steve C.F.
, p. 4565 - 4573 (2004)
The structurea€"activity requirement of the PP2A-inhibiting demethylcantharidin for the circumvention of cisplatin cross-resistance demonstrated by the novel TCMa€"Pt compounds is discussed. Novel TCM-platinum compounds [Pt(C8H8O5)(NH 2R)2] 1-5, derived from integrating demethylcantharidin, a modified component from a traditional Chinese medicine (TCM) with a platinum moiety, possess anticancer and protein phosphatase 2A inhibition properties. The compounds are able to circumvent cisplatin resistance by apparently targeting the DNA repair mechanism. Novel isosteric analogues [Pt(C9H 10O4)(NH2R)2] A and B, devoid of PP2A-inhibitory activity, were found to suffer from an enhanced DNA repair and were cross-resistant to cisplatin. The results advocate a well-defined structure-activity requirement associating the PP2A-inhibiting demethylcantharidin with the circumvention of cisplatin cross-resistance demonstrated by TCM-Pt compounds 1-5.
Diels-Alder adducts of maleic anhydride and dienes: New compounds by crystallization
Bolte, Michael,Degen, Alexander,Egert, Ernst
, p. 1338 - 1342 (2000)
We have determined the crystal structures of bicyclo[2.2.1]hept-2-ene-endo-cis-5,6-dicarboxylic anhydride, C9H8O3, (I), 1,2,3,4,7,7-hexachlorobicyclo [2.2.1]hept-2-ene-endo-cis-5,6-dicarboxylic anhydride diethyl ether solvate, C9H2Cl6O3·0.16-C4H10O, (II), bicyclo[2.2.1]hept-2-ene-endo-cis-5,6-dicarboxylic acid, C9H10O4, (III), 1,2,3,4,7,7-hexachlorobicyclo [2.2.1]hept-2-ene-endo-cis-5,6-dicarboxylic acid, C9H4Cl6O4, (IVa) and (IVb), and ethyl 1,2,3,4,7, 7-hexachloro-6-carboxybicyclo[2.2.1]hept-2-ene-endo-cis-5-carboxylate monohydrate, C11H8Cl6O4·H2O, (V). Compounds (I) and (II) were prepared by a standard Diels-Alder reaction from maleic anhydride and cyclopentadiene or hexachlorocyclopentadiene, respectively. The crystal-growing processes of these compounds led to surprising results: rapid recrystallization of (I) from diethyl ether and (II) from petroleum ether gave crystals of these compounds, however, crystallization by slow evaporation techniques using common solvents yielded new compounds in which the five-membered heterocycle has been cleaved.
Synthesis of new N-norbornylimide substituted amide derivatives, their reductive Heck and domino Heck reactions
Albayrak, Fatma,Gunkara, Omer Tahir,Ersoy, Elif Basak,Ocal, Nuket,Kaufmann, Dieter E.
, p. 244 - 256 (2017)
Palladium-catalyzed, regioselective hydroarylation reactions of N-norbornenylimide substituted amides were studied to synthesize pentanamide derivatives containing exo-aryl-substituted norbornyl imide groups in excellent yields. All newly synthesized derivatives have been characterized by FTIR, 1H, 13C NMR, GC/MS and TOF/Qtof analyses.
Tsutsui et al.
, p. 5233,5235 (1969)
Application of arylboron difluoride Lewis acid catalysts to the Diels- Alder reaction: Convenient, non-volatile alternatives to boron trifluoride
De La Torre, Maria Fe,Caballero, M. Cruz,Whiting, Andrew
, p. 8547 - 8554 (1999)
Comparative studies were carded out on boron trifluoride etherate, phenylboron difluoride and meta-nitrophenylboron difluoride for the Lewis acid catalysed Diels-Alder reaction of cyclopentadiene and a range of standard dienophiles in tetrahydrofuran solution. Phenylboron difluoride showed remarkably similar reactivity in terms of yield and endo to exo selectivity to boron trifluoride, whereas meta-nitrophenylboron difluoride was more reactive than either boron trifluoride or phenylboron difluoride and showed more marked differences in endo: exo ratios. These results contrast to some extent with gas-phase semi-empirical calculations (PM3), which suggest that boron trifluoride and meta-nitrophenylboron difluoride should have similar reactivity; phenylboron difluoride being less reactive. However, since arylboron difluorides are easily prepared, these Lewis acids represent a group of potentially highly tuneable catalysts for Diels-Alder reactions.
Hydroarylation reactions of N-acylaminosubstituted tricyclic imides
Gul, Melek,Kulu, Irem,Ocal, Nuket
, p. 345 - 350 (2013)
The palladium-catalysed hydroarylation of unsaturated N-acylamino- substituted tricyclic imides provided a new stereoselective synthesis of exo-aryl(heteroaryl)-substituted tricyclic N-acylamino imides.
Application of olefin metathesis for the synthesis of constrained β-amino esters from norbornenes
Nadany, Adam E.,Mckendrick, John E.
, p. 2139 - 2141 (2006)
Synthesis of a number of novel, conformationally rigid β-amino esters has been achieved via a tandem olefin metathesis reaction. The starting materials are readily accessible from the Diels-Alder adduct between cyclopentadiene and maleic anhydride. Georg Thieme Verlag Stuttgart.
Anion recognition using preorganized thiourea functionalized [3]polynorbornane receptors
Pfeffer, Frederick M.,Gunnlaugsson, Thorfinnur,Jensen, Paul,Kruger, Paul E.
, p. 5357 - 5360 (2005)
(Chemical Equation Presented) A new family of [3]polynorbornane frameworks exhibiting conformationally preorganized aromatic thiourea (cleft-like) receptors have been designed and synthesized for anion recognition. These show excellent affinity for the biologically relevant dihydrogenphosphate (H 2PO4-) and dihydrogenpyrophosphate (H 2P2O72-) anions (among others), which are bound in 1:1 and 2:1 (host:anion) ratio, respectively. Moreover, visually striking color changes accompany guest binding, enabling this family to act as colorimetric anion sensors.
Preparation method of exo-Dickson anhydride
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Paragraph 0017-0018; 0042-0043; 0046-0049, (2021/10/16)
The preparation method comprises the following steps: (1) adding a solvent in a reaction container, maleic anhydride, a chiral catalyst D and nitrogen to replace air in a reaction container. (2) At -5 - 5 °C, cyclopentadiene is added dropwise, and the dropping is carried out at a certain temperature. (3) After the completion of the reaction, water was added and quenched. Concentration, crystallization in ethanol and filtration gave exo. The preparation method has the characteristics of high reaction stereoselectivity, high yield, good product quality, simple and convenient process operation, high stability and high safety, and is suitable for industrial mass production.
Synthesis of 4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione derivatives as lead scaffolds for neuroprotective agents
Egunlusi, Ayodeji O.,Malan, Sarel F.,Joubert, Jacques
, p. 17 - 27 (2020/10/30)
Neurodegenerative disorders are characterised by progressive loss of neuronal functions. Of the proposed mechanisms, excitotoxicity, mediated by prolonged glutamate activation and calcium overload, is prominent. NGP1-01, a polycyclic cage amine, and tricyclo[6.2.1.02,7]undec-9-ene-3,6-dione have been shown to display calcium-modulating properties. In this study, we synthesised structurally-related 4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione as the base scaffold, and incorporated various functional moieties through aminolysis, to afford a series of imide derivatives. All final compounds were obtained in yields between 47-97% and their structures were confirmed by NMR, IR and MS. These structurally-related derivatives could potentially act as neuroprotective agents. Additionally, their synthetic versatilities could make them precursors, as lead compounds, to potential pharmacologically-active agents.
